20VC: Canva Co-Founder, Cliff Obrecht on The Journey From 100 VC Rejections to a $40BN Company, Why Good Enough is Not Good Enough, The Secret to Hiring Non-Obvious Talent and Relationships to Money and Why They Are Giving Away Billions

20VC: Canva Co-Founder, Cliff Obrecht on The Journey From 100 VC Rejections to a $40BN Company, Why Good Enough is Not Good Enough, The Secret to Hiring Non-Obvious Talent and Relationships to Money and Why They Are Giving Away Billions

Cliff Obrecht is the Co-Founder & COO @ Canva, the free-to-use online graphic design tool that makes it easy for anyone to design anything from presentations to videos and social media. Cliff and Mel have scaled Canva to over 60 million monthly users, 2,000 employees, and 500,000 teams from companies like Intel and Zoom using Canva. During this incredible growth journey, they have raised over $580M with their last round valuing the company at over $40BN.

In Today's Episode with Cliff Obrecht

1.) From Teacher to Billionaire Tech Founder:

  • How did Keith make his way into the world of tech with his founding of FusionBooks? What did the process with FusionBooks teach him about how to run Canva?
  • How did the early fundraising days for Canva go? Why does Cliff think they got over 100 no's?
  • What are Cliff's biggest pieces of advice for founders today, not in Silicon Valley, looking to raise from Silicon Valley VCs?

2.) Scaling to $40BN: The Biggest Lessons:

  • What does Cliff mean when he says the secret to successful hiring is looking for "distance traveled"? How does he determine this in the interview process?
  • What have been some of the single biggest lessons in what it takes to acquire the best talent?
  • What are some of the biggest mistakes Cliff has made in talent acquisition? How has his process changed as a result?
  • What do Canva do to get the best operators as advisors in the company? How do they compensate these advisors? What does Cliff advise founders on how to do the same?

3.) The Art of Deal-Making:

  • How does Cliff think through what makes a "good deal"? How does he approach negotiation?
  • What are the biggest mistakes founders make when negotiating and doing deals?
  • What have been Cliff's biggest lessons on successful investor relations over the years?
  • How does Cliff and Canva approach acquisitions? What do they look for? What is their process? Why do most tech companies approach acquisitions the wrong way?

4.) Cliff Obrecht: Money, Fatherhood and Marriage:

  • How does Cliff analyze his relationship to money today? How much money is enough? How has his relationship to money changed over time?
  • Why have Cliff and Mel given away over $10BN to their foundation? Why is philanthropy so hard to do effectively?
  • Why would Cliff hate for his children to be brought up in excess wealth?
  • What does "great fatherhood" mean to Cliff? What are the most challenging aspects of parenting?
  • What are the secrets to a happy marriage? How does co-founding a company with your other half work well? How does it work poorly?

Episoder(1403)

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20Sales: The Best Sales People Are F***** in the Head | The Unspoken Truths All Sales Leaders Need to Know in 2026 | Why Europe is a Nightmare for Recruiting | How to Improve Sales Team Performance in 24 Hours with Chad Peets

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9 Jan 1h 9min

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20VC: $0-$260M in Revenue in Three Years: How We Did It | You Need to Work Weekends to Win — Most Founders Aren't Ambitious Enough | The Revolut Playbook: Speed, Urgency, Extreme Ownership, and Zero Excuses with Alan Chang @ Fuse Energy

I have interviewed 1,000 entrepreneurs over 10 years. Nik Storonsky and our guest today are the two best that I have interviewed.  Joining the show today; Alan Chang, Co-Founder and CEO of Fuse Energy. Alan has scaled Fuse Energy from $2M in revenue in the first year, to $20M the second year to now $400M in the third year. Like Netflix beat incumbents to own media, Revolut beat incumbents to own banking, Fuse will beat incumbents to own energy. Prior to founding Fuse, Alan was one of the first three hires at Revolut where he played a crucial role alongside Nik (Founder) in scaling the company to over $75BN valuation.  AGENDA: 00:04:00 — The interview process that led to the $150M pay packet 00:05:05 — The moment I knew Revolut was going to be a $TRN company 00:06:10 — How Revolut drove speed and urgency in their teams 00:07:35 — Biggest lesson from Nik Storonsky @ Revolut 00:09:40 — If you want to build a generational company, you cannot have work-life balance 00:11:40 — What I disagreed with Nik @ Revolut on most 00:13:35 — Is Nik right that Revolut should have got a banking licence earlier? 00:15:05 — The green movement and the idea of "using less" is BS 00:22:55 — Why China is the shining light for regulation to follow 00:33:00 — What Nik at Revolut taught me about ownership and excuses 00:34:50 — The signs of truly top performing people in a team 00:36:55 — We do not have enough ambitious founders — we need to do more, not focus 00:39:55 — You need to work weekends to win 00:43:50 — Every single year we 10x revenue — now at ~$400M 00:44:35 — Why Eastern European engineers are the best Items Mentioned in Today's Show: Try NEXOS.AI for yourself with a 14-day free trial: https://nexos.ai/20vc

5 Jan 56min

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Matt Fitzpatrick is the CEO of Invisible Technologies, leading the company's mission to make AI work. Since joining as CEO in January 2025, he has raised $100M and accelerated AI adoption across industries from sports to consumer and government. Previously, Matt was a Senior Partner at McKinsey, where he led QuantumBlack Labs, the firm's AI R&D and software development arm. AGENDA: 04:40 Interview with Matt Fitzpatrick: Career Journey and Leadership 09:35 The Single Biggest Barriers to Enterprises Adopting AI 15:26 It is BS That Enterprises Can Adopt AI Without Forward-Deployed Engineers 28:05 Are AI Talent Marketplaces Dead? What is the best model? 46:33 How Does the Data Labelling Market Shake Out: Who Wins/ Who Loses 48:27 Are Revenue Numbers for Data Labelling Real Revenue? Or GMV? 51:20 Best Capital Allocation Decision? What did Matt Learn from it? 53:19 How Important is Brand for AI Companies Selling Into Enterprise? 01:05:59 Remote Work vs. In-Person Collaboration 01:17:06 What Does No-One Know About the Future of AI That Everyone Should Know

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20VC's Big Fat Quiz of the Year: Founder, Fund and Breakout Company of 2025 | Predictions for 2026: The Company to Buy, The Biggest Short | Why Salesforce Could Win 2026 and The Tailwinds NVIDIA Will Face

20VC's Big Fat Quiz of the Year: Founder, Fund and Breakout Company of 2025 | Predictions for 2026: The Company to Buy, The Biggest Short | Why Salesforce Could Win 2026 and The Tailwinds NVIDIA Will Face

AGENDA: 03:48 Founder of the Year 2025 06:58 Product of the Year 10:05 Fund of the Year 20:52 Breakout Companies of 2025: Who Made the Biggest Impact? 26:57 Biggest Surprises of 2025 32:57 Predictions for 2026: Top Performing Tech Stocks of the Year 35:25 B2B Stocks to Watch 38:31 Why Salesforce Could Be the Buy of 2026 47:11 Google, Meta, Apple, NVIDIA, Microsoft: Buy One, Short One 55:38 IPO Speculations: Who Will Go Public in 2026 01:00:57 The Impact of AI on Employment

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20Product: On Running's CPO on How to Create Emotion Through Product | Why 99% of Products Fail and How to Create Cults Around Products | The Biggest Product Mistakes On Have Made & Lessons Learned with Gérald Marolf

20Product: On Running's CPO on How to Create Emotion Through Product | Why 99% of Products Fail and How to Create Cults Around Products | The Biggest Product Mistakes On Have Made & Lessons Learned with Gérald Marolf

Gérald Marolf is the Chief Product Officer at On Running. Gérald oversees the full range of On's shoes, apparel and accessories to make sure each delivers performance, comfort and style. Before On, Gérald spent over a decade building consumer brands with collaborators such as Microsoft and Ferrari. AGENDA: 00:00 – Why Most "Great Products" Fail to Create Emotion 03:00 – How Perfume Taught Me Everything About Desire & Product 06:10 – The Brutal Reality of Building Physical vs Digital Products 16:00 – Why "Simple Design" Is Overrated and Dangerous 23:00 – Why Vuori is the Brand to Short in Consumer  28:30 – The Biggest Product Mistake: Listening to Customers Too Much 32:10 – On Only Do Tennis Because of Roger Federer 38:30 – Were We Too Late to Marathon Running? A Painful Admission 43:40 – The Most Controversial Product On Has Ever Launched 49:00 – Are Counterfeits Good or Bad in Fashion?

19 Des 202556min

20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

20VC: Will SpaceX IPO at $1.5TRN | Will Cursor Kill Figma | Lightspeed Raises $9BN | OpenAI: $1BN from Disney, New CRO & #1 App in App Store | Oracle and Broadcom Hit: Now the Time to Buy?

AGENDA: 03:32 Lightspeed's $9 Billion Fundraise 05:20 The Impact of Mega Funds on Seed VCs 10:09 The Supercycle of Growth and Late-Stage Investments 13:06 Disney Invests $1BN into OpenAI and What It Means 23:19 Oracle Hit Hard: Is Now the Time to Buy 28:34 Broadcom's Market Cap Drop and Anthropic's AI Chip Orders 35:04 Cursor Competes with Figma: The Convergence of Design and Coding Tools 46:20 The Biggest Danger for Incumbents: Being Maimed by AI 55:28 Boom Supersonic Raising $300M to… Power Data Centres… WTF 01:00:24 Will SpaceX IPO at $1.5TRN and The Elon Option Value

18 Des 20251h 22min

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